HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzoic Acid → 2-Phenyl-4,5-dihydro-1,3-thiazole-4-carboxylic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzoic Acid | HCID 243 | — |
| Reactant | D-Cysteine | HCID 92851 | — |
| Product | 2-Phenyl-4,5-dihydro-1,3-thiazole-4-carboxylic acid | HCID 88327 | — |
Reaction Steps
(S)-Cysteine is reacted with benzoic acid to form 2-phenylthiazoline-4-carboxylic acid. 2-Phenylthiazoline-4-carboxylic acid is amidated with 4-benzyloxazolidone. The amidated 2-phenylthiazoline-4-carboxylic acid is alkylated with methyl iodide in the presence of TiCl4 and lithium diisopropylamide. The alkylated species is hydrolyzed by lithium hydroxide in methanol to obtain (S)-2-methylcysteine methyl ester.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06903220B2 |
| Source dataset | uspto-grants-2005_06 |
| ORD ID | ord-99ca2f45168a4d2f8248d2ab4ec95465 |
| Source note | uspto-grants-2005_06 |